diff --git a/src/parser/paragraph.rs b/src/parser/paragraph.rs
index a6af51d..a580596 100644
--- a/src/parser/paragraph.rs
+++ b/src/parser/paragraph.rs
@@ -1,5 +1,4 @@
 use nom::branch::alt;
-use nom::character::complete::line_ending;
 use nom::combinator::eof;
 use nom::combinator::peek;
 use nom::combinator::recognize;
@@ -14,6 +13,7 @@ use crate::parser::parser_context::ContextElement;
 use crate::parser::parser_context::ExitMatcherNode;
 use crate::parser::parser_with_context::parser_with_context;
 use crate::parser::util::exit_matcher_parser;
+use crate::parser::util::start_of_line;
 
 use super::element::non_paragraph_element;
 use super::error::Res;
@@ -32,14 +32,10 @@ pub fn paragraph<'r, 's>(context: Context<'r, 's>, input: &'s str) -> Res<&'s st
     let exit_matcher = parser_with_context!(exit_matcher_parser)(&parser_context);
 
     let (remaining, (children, _exit_contents)) = verify(
-        many_till(
-            standard_set_object_matcher,
-            peek(alt((eof, recognize(tuple((line_ending, exit_matcher)))))),
-        ),
+        many_till(standard_set_object_matcher, peek(recognize(exit_matcher))),
         |(children, _exit_contents)| !children.is_empty(),
     )(input)?;
 
-    let (remaining, _linebreak) = alt((eof, line_ending))(remaining)?;
     let source = get_consumed(input, remaining);
 
     Ok((remaining, Paragraph { source, children }))
@@ -48,8 +44,9 @@ pub fn paragraph<'r, 's>(context: Context<'r, 's>, input: &'s str) -> Res<&'s st
 #[tracing::instrument(ret, level = "debug")]
 fn paragraph_end<'r, 's>(context: Context<'r, 's>, input: &'s str) -> Res<&'s str, &'s str> {
     let non_paragraph_element_matcher = parser_with_context!(non_paragraph_element)(context);
+    let start_of_line_matcher = parser_with_context!(start_of_line)(&context);
     alt((
-        recognize(many1(blank_line)),
+        recognize(tuple((start_of_line_matcher, many1(blank_line)))),
         recognize(non_paragraph_element_matcher),
         eof,
     ))(input)
diff --git a/src/parser/plain_list.rs b/src/parser/plain_list.rs
index f3e077f..b0a0a60 100644
--- a/src/parser/plain_list.rs
+++ b/src/parser/plain_list.rs
@@ -16,8 +16,10 @@ use crate::parser::util::start_of_line;
 use nom::branch::alt;
 use nom::bytes::complete::tag;
 use nom::character::complete::digit1;
+use nom::character::complete::line_ending;
 use nom::character::complete::one_of;
 use nom::character::complete::space0;
+use nom::character::complete::space1;
 use nom::combinator::eof;
 use nom::combinator::recognize;
 use nom::combinator::verify;
@@ -57,20 +59,38 @@ pub fn plain_list_item<'r, 's>(
 
     let element_matcher = parser_with_context!(element)(&parser_context);
     let exit_matcher = parser_with_context!(exit_matcher_parser)(&parser_context);
-    let (remaining, (bull, _ws)) = tuple((bullet, space0))(remaining)?;
-    let (remaining, (contents, _exit_contents)) =
-        many_till(element_matcher, exit_matcher)(remaining)?;
-    let source = get_consumed(input, remaining);
-
-    Ok((
-        remaining,
-        PlainListItem {
-            source,
-            indentation: indent_level,
-            bullet: bull,
-            contents,
-        },
-    ))
+    let (remaining, bull) =
+        verify(bullet, |bull: &str| bull != "*" || indent_level > 0)(remaining)?;
+    let maybe_contentless_item: Res<&str, &str> = alt((eof, line_ending))(remaining);
+    match maybe_contentless_item {
+        Ok((rem, _ws)) => {
+            let source = get_consumed(input, rem);
+            return Ok((
+                rem,
+                PlainListItem {
+                    source,
+                    indentation: indent_level,
+                    bullet: bull,
+                    contents: Vec::new(),
+                },
+            ));
+        }
+        Err(_) => {
+            let (remaining, _ws) = space1(remaining)?;
+            let (remaining, (contents, _exit_contents)) =
+                many_till(element_matcher, exit_matcher)(remaining)?;
+            let source = get_consumed(input, remaining);
+            return Ok((
+                remaining,
+                PlainListItem {
+                    source,
+                    indentation: indent_level,
+                    bullet: bull,
+                    contents,
+                },
+            ));
+        }
+    };
 }
 
 #[tracing::instrument(ret, level = "debug")]
@@ -188,4 +208,28 @@ mod tests {
         assert_eq!(remaining, "");
         assert_eq!(result.source, "1. foo");
     }
+
+    #[test]
+    fn plain_list_cant_start_line_with_asterisk() {
+        // Plain lists with an asterisk bullet must be indented or else they would be a headline
+        let input = "* foo";
+        let initial_context: ContextTree<'_, '_> = ContextTree::new();
+        let document_context =
+            initial_context.with_additional_node(ContextElement::DocumentRoot(input));
+        let plain_list_matcher = parser_with_context!(plain_list)(&document_context);
+        let result = plain_list_matcher(input);
+        assert!(result.is_err());
+    }
+
+    #[test]
+    fn indented_can_start_line_with_asterisk() {
+        // Plain lists with an asterisk bullet must be indented or else they would be a headline
+        let input = " * foo";
+        let initial_context: ContextTree<'_, '_> = ContextTree::new();
+        let document_context =
+            initial_context.with_additional_node(ContextElement::DocumentRoot(input));
+        let plain_list_matcher = parser_with_context!(plain_list)(&document_context);
+        let result = plain_list_matcher(input);
+        assert!(result.is_ok());
+    }
 }
diff --git a/toy_language.txt b/toy_language.txt
index de546e9..c506087 100644
--- a/toy_language.txt
+++ b/toy_language.txt
@@ -1,3 +1,24 @@
+prologue *goes here* I guess *bold
+text*
+
+bold*wont* start *or stop*when there is text outside it
+
+I guess *regular
+
+text*
+
+[foo *bar] baz* car
+
+
+*nesting *bold entrances* and* exits
+
+* Heading
+
+body of heading
+
+** Child heading
+** Immediate second child heading
+
 * Second top-level heading
 foo bar
 1. This is a list immediately after a paragraph